I would think a Harley Rake would work well AFTER scalping the surface with some kind of mower, perhaps just a regular lawn mower. You will have to choose the "right moment". Do not cultivate wet soil, soil needs to be moist but not wet.
Read the archive threads so determine was has been successful for others.
If Massey 1135 in your profile is a Skid Steer, rather than a tractor, add that information.
You would know better than I if small wheels on your Skid Steer, relative to a tractor, will rut the ground further. A tracked Skid Steer would be fine.